How to be a digital nomad and why it’s life-changing

Globetrender’s editor Jenny Southan speaks to three digital nomads about why they decided to give up their nine-to-five office jobs in favour of working remotely from different parts of the world – from Melbourne and Santiago, to Los Angeles and Bali.

Give us some background on what you do?

I started out in New York on an international internship at a Wall Street Bank. I then spent seven years at a political risk consultancy working in Russia, Asia, the US and the Middle East, and ended up based in London. I finished a masters degree at Cambridge in 2013 and realised that despite my relative success, I was unhappy: I had back trouble, no creative outlet, and was frustrated and stressed.

I decided that I wanted to a) run my own business, b) Get out of London, and c), be outside more. This pushed me to apply for the job of setting up the Intern Group Australia. I was based in Melbourne for four years and was location independent as that company took off. I then decided I wanted to learn Spanish and felt like a new challenge so moved to Santiago in November 2017 to head up the programmes for the Intern Group worldwide.

The Intern Group partners with universities, young people and career changers giving them the opportunity to live in a new country while gaining experience in their chosen field. We operate in nine cities around the world. I am accountable for these offices and the ten more we are opening by 2020.

What do you value in not being tied to one place and spending a lot of time on the road or living in different countries?

Is there anything you miss about the security of an office job? Would you ever go back to that way of living?

No and No.

Describe a typical working day for you as a digital nomad? How important is routine?

Routine is important when you are constantly moving. I read and write every day, work out every other day, have weekly meetings with direct reports and our CEO, and a quarterly meeting with the entire management team. All of this is done online with Google Hangouts, and we have AGM in person at a new city each year. At the personal level, I Skype and Whatsapp a lot. I make the effort to visit people at home. Each year I make sure I spend Christmas with my mum – this year we went to Buenos Aires.

What does 2018 look like for you in terms of the places you will be travelling to and projects you will be working on?

I spent New Year’s here in Santiago then went back to Australia to catch up with the team there. Then I am going to New Zealand to plan our Kiwi office, then on to Thailand for a holiday with some old friends and to do some diving. I’ll be back in Santiago for April for work on technical projects, and in the UK for the summer before our AGM in New York in October.

What writers have most inspired you?

On how to be: Seneca, La Montaigne.

On how to think: Tolle, Camus.

On how to work: Ferriss, Godin.

In living a relatively minimalist life, how has your relationship to material possessions and ownership changed?

After being let down by someone I was close to, I gave almost all my stuff away. I have lived in Airbnb’s and travelled ever since. I have learnt Spanish, have a better job, set up a charitable partnership with my company, become a Chilean resident, and have spent time and made friends and had fun in Thailand, Australia, Indonesia, Colombia, Chile, Argentina, Spain, Portugal, France and England.

I used to live in a world of things and now I live in a world of experience. Stuff – bills, commuting, office politics, winter, TV, mediocrity are gone now. It’s simple, clean, human, better. In falling out of love with one person, I fell in love with the world.

Where do you call home?

I’m a Chilean resident. It’s a friendly country with an unfair share of beautiful beaches and lakes. But home is wherever the kettle’s on.

What would you say to someone who is dreaming about packing it all in and becoming a digital nomad?

Go. The pound is getting weaker and you’re getting older. Buy a plane ticket for six months from now then work backwards from there.

What challenges/realities do people need to be aware of?

It’s lonely at times. You have to be able to engage with strangers. To trust that you’ll be okay. Once you leave, base all your decisions on hope rather than fear. I gambled it all, twice on a new country and a new job. Both times I was terrified and both times it was a total win.

What motivated you to become a digital nomad?

I wanted to spend more time writing novels, and be in charge of my own schedule – of what I did and didn’t say yes or no to. I’ve never entirely loved the office environment because I don’t find it creatively stimulating (at least not the offices I worked in) and I’m lucky in that I’m pretty disciplined and self-motivated, and I genuinely also thought I’d get more done. I also liked the freedom that came with it – as long as I had my laptop and an internet connection, I knew I could work from anywhere.

Describe your relationship with LA and what first inspired you to spend a month working out there?

I’d only ever been to LA for brief press trips until 2015, when I had a week’s holiday with friends in the city. I loved it almost immediately – the sunshine, of course, but also the pace of life and the sense that the hierarchies in America are a lot flatter than in the UK, where the class system is still so embedded. I could pick up a phone and get a meeting with someone really easily (the British accent helps) and that is very appealing for a journalist.

After that week’s stay, I pitched the idea of living there for six months to The Observer, where I was a staff feature writer. I knew that most British writers gravitated towards New York, whereas actually having someone on-site on the West Coast for running stories and movie junkets would be appealing to my editors. They agreed to three months and I paid my own way – booked my flight, covered the Airbnb – so really they were getting a good deal.

I loved working in LA because you can do so much of it outside – typing is much more fun when you’re in the sunshine on the patio of your local cafe. I also really enjoyed the time difference. You wake up to a morning panic and a barrage of emails because the UK is eight hours ahead, but once you’ve dealt with that, your afternoons are blissfully quiet and free of email, so you can really knuckle down and get stuff done.

I also enjoyed the physical side of LA life – the beautiful hikes you can do, the yoga, the spin classes. As a writer, you can spend so much time at your desk, hunched over your laptop, that it’s good to sometimes be *in* your body gain and LA is totally geared up for that.

How does your working day differ in LA compared with London?

As above, really – the mornings are always very busy because you’re dealing with emails and phone calls on a UK time-zone. But then in the afternoon, I’ll be left to my own devices to interview, report or write. The main difference – and it sounds silly, but it really does have a massive impact – is that I drive everywhere so I never take public transport. I know I can get most places in LA in half an hour in the car (rush hour notwithstanding) and can take everything I need with me without having to worry about carrying it all day and that takes away a major source of stress. I realise it’s rubbish for the environment though.

When working abroad, is there a risk of feeling and behaving like you’re on holiday? Does that matter?

Yes, it’s an interesting one, especially in LA because the weather is so good. I found that, about six weeks into my first stint in LA, I was exhausted but didn’t understand why. Then I realised I’d been working extremely hard but hadn’t thought to notice it because the sun was shining. I took myself off for a weekend to Santa Barbara as it was really necessary for me to recuperate.

I’ve never had the thing of not doing my work because I want to sunbathe though. Like I said, I’m a strict self-disciplinarian.

What were you working on during your most recent stint in LA?

I went there to meet a book deadline and finish the first draft of a memoir I’ve been ghosting. While I was there, I was also commissioned to interview Rosie Huntington-Whiteley for Harper’s Bazaar in the UK, and to write a few columns for The Telegraph, but I didn’t want to take on too many journalistic commissions so deliberately turned some down.

What are the main challenges of being a freelancer?

Worrying about where your next pay cheque is coming from and remembering to put aside enough money for grown-up things like tax and a pension. I personally also find one of the biggest challenges is knowing when to say no. When I first started freelancing, I said yes to absolutely everything because I was so panicked about earning enough to pay the rent. I’ve become a bit more discerning. I think the key is working out what is good for you and what is good for you bank balance. If a commission doesn’t fall into one of those two categories, it’s probably worth passing on.

What would you say to someone who is dreaming of giving up their job and becoming a digital nomad?

I can’t recommend it highly enough. I’ve felt liberated and empowered by my decision. It is a big leap of faith, but if you’re not going to take a gamble on yourself, then who is?

Alex Holder, journalist, writer, mother

Describe the journey you went on from working in advertising to temporarily relocating to Bali?

I worked up to the top of advertising, being made partner and executive creative director at Anomaly at 30. I had one of those cliche epiphanies that happen to women after they have a kid – I suddenly realised that I was ploughing a lot of energy into something I didn’t really care about, I wanted to work on things I was passionate about but as a partner in an agency you have to be all things to all clients.

So I quit full-time work, and now in-between contracts at wonderful places such as ELLE, Warner Music and Dazed, I have enough time to write more of my own work and see my son. I’m a freelancer – I would never use the title “digital nomad”.

What motivated you to make those changes to your life/career?

I wanted to see my toddler son when he was awake and also have time to breath and think, not just be on a treadmill to the end of the week all the time.

What are the benefits of being a freelancer?

The benefits are getting to change up my environment. I get bored easily and like new people and new goals. I love that my work now is task based and I can feel a sense of completion when I hand something in. Whereas with a full time job it felt relentless, like the work was never done.

Also working from home which I love – I’m so much more productive there than anywhere else – and I get to put a wash load on while I work. I stewed a pear for my breakfast the other day – no one gets to do that if you have to be on the Victoria line at 8.45am.

What are you working on at the moment?

I’ve just finished a couple of months at Warner Music writing TV formats – I was based in their offices for that. I’m now in Bali and writing some features for London publications and working remotely for Anomaly advertising agency on a fun project.

How important is creating a routine?

So important. My first few weeks in Bali were chaotic and messy because we couldn’t find a place to work which had both a good desk and good wifi. Also child care was a little sporadic, which meant that grabbing an hour here or there to work meant we were so unproductive. Also it’s too easy to go into holiday mode if you don’t carve out work time.

What does a a typical day look like for you in Bali?

A working day:

We wake up at 6am and have breakfast with our son. At 10am a nanny comes and we go to a work hub (there are a few out here) or local cafe where we work at our computers for a few hours. The nanny goes at 4pm and then it’s family pool time or dinner at a beach club.

How have your priorities changed in recent years?

I value time over money now. I would always rather more time to spend with my son or to spend on passion projects that don’t pay much than earn more money. When I spend, I always equate things with time: ‘Are these jeans worth half a day in an office in Kensington?’

What challenges have you faced in this new way of living and working?

The hustle is hard. Lots of work comes from doing good work, but invariably as a freelancer I have to get in touch with people and send emails that feel out of my comfort zone as it’s the only way to let people know you are available to work.